The present invention discloses an asymmetrically end capped polyolefin which has a phenyl-glycidyl-ether end group at one end of the polyolefin and a halogen atom at the other end and its use as a macromonomer in copolymerization.
In U.S. Pat. No. 3,060,140, Greenlee discloses the use of glycidyl-ether modified polybutadiene molecules. Greenlee achieved this modification by reacting polybutadiene with phenol in the presence of a Lewis acid catalyst such as BF.sub.3. These functionalized butadienes could then be polymerized by standard techniques with such monomers as halohydrins using standard polymerization techniques.
Wismer et al. in U.S. Pat. No. 3,154,599 discloses the use of epoxy or phenyl-glycidyl-ether terminated epoxy resins for use in coating compositions. The phenyl-glycidyl-ether compounds of this patent are relatively low molecular weight bis epoxides for use in epoxy resin formation.
Clemens in U.S. Pat. No. 3,183,281 described the use of bis(phenyl-glycidyl-ethers) terminated polymers to form a poly epoxide. These epoxides are used in a composition comprising other types of polymers and used as an agent to form coating materials.
Domeier in U.S. Pat. No. 4,524,162 used difunctional epoxides based on phenyl-glycidyl-ethers and various other difunctional epoxides as reagents in forming particular types of polyacrylic epoxides for the use in injection molded curable thermoset resins.
Kennedy et al. in U.S. Pat. No. 4,429,009 disclosed the manufacture of phenyl-glycidyl-ethers terminated polyisobutylene for use in epoxide cure systems. All the above uses of the phenyl-glycidyl-ether constituent groups on the end or substituted onto specific types of polymers, were used to form either epoxy networks or were used to form certain types of copolymers involving indiscriminate addition of phenyl-glycidyl-ethers onto such polymers as polybutadiene. Although the Kennedy patent does disclose the manufacture of phenyl-glycidyl-ether modified polyisobutylenes, all the end groups of the polyisobutylene polymers were functionalized with phenyl-glycidyl-ether end groups.
Thus, all of the above patents describe the use of bis or poly phenyl-glycidyl-ether functionalized polymers as polymerization agents or network forming agents. There is no mention or indication in any of these patents that a macromonomer of polyisobutylene could be prepared having an active, polymerizable end group of a phenyl-glycidyl-ether with the other end being a chlorine atom. That is, none of the above patents teaches the ability to make asymmetrically terminated polyisobutylene where one end has a chlorine atom and the other end has a phenyl-glycidyl-ether group.
It is desirable to manufacture .alpha.-phenyl-glycidyl-ether-.omega.-chloro polyolefin macromonomers for use in copolymerization processes utilizing ring opening polymerization in the presence of polymerizable monomers such as halohydrins and simple alkyl epoxides. These copolymers could have wide utility in a number of areas including: emulsifying agents because the resulting copolymer would have a large polyisobutyl hydrophobic segment and polyether hydrophilic segment; compatibilizing agents in rubber-polymer blends and composites where one of the composite materials is a polyester fibrous material and the other is an elastomeric material such as a standard elastomer including natural rubber, polyisobutylene, polybutadiene and polyisoprene; or molecular composite components for compositions requiring excellent environmental stability and excellent damping and air retention properties.